Potassium Carbonate → HCID 22241343, compound

HRID 892218Notes

Reaction equation

HRID 892218 reaction equation
[OH:1][CH2:2][C:3]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=1.[CH3:19][N:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=[C:21]1[CH2:31]Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[OH:1][CH2:2][C:3]1[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:10]=[CH:11][CH:12]=1)[O:13][CH2:31][C:21]1[N:20]([CH3:19])[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 88996682-(chloromethyl)-3-methylquinazolin-4(3H)-oneHCID 22241484HCID 22241484, compound

Product 1

HCID 22241343HCID 22241343, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(2-hydroxymethyl-3-methyl-benzyloxy)-phenol (87 mg, 0.38 mmol, example 100) and (3-methyl-4-oxo-3,4-dihydro-quinazolin-2-yl)-methyl chloride (94 mg, 0.45 mmol, example 99) in DMF (1 mL) is added powdered K2CO3 (78 mg, 0.5 mmol). The resulting mixture is warmed to 60° C. and stirred at this temperature for 5 h. This mixture is cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried over MgSO4 and concentrated. The residue is purified by flash chromatography (silica, 40% ethyl acetate/30% dichloromethane in hexanes) to give the title compound as a foam. MS (ESI) 417 (M+H)+.

Workup

  1. temperatureThis mixture is cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography (silica, 40% ethyl acetate/30% dichloromethane in hexanes)

Sources & evidence

ORD record
ord-bffe8e2e507f444fba1cdd8abed06a94
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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